Plastic Lens Polymerization: Nonhalogenated Tin Catalyst and Diketone Control

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Solution Overview

Problem

Polythiourethane-based lenses prepared with amine-based catalysts exhibit color issues, leading to reduced total transmittance, and nonhalogenated tin-based catalysts face challenges in maintaining sufficient pot life and stability.

Innovation Solution

A polymerizable composition comprising a bi- or higher functional isocyanate compound, a bi- or higher functional thiol compound with sulfide or ester bonds, a nonhalogenated tin-based catalyst, and a diketone-based low-temperature reaction rate controlling agent, which controls reactivity and viscosity to enhance transparency and workability.

Engineering Contradictions & Design Principles

VSEngineering Contradiction Analysis

1Productivity

If amine-based catalysts are used for polymerization, then polymerization activity is improved, but the resulting lens exhibits color issues and reduced total transmittance

Engineering Contradiction:
Improvepolymerization activityVSAvoidcolor and transmittance
Core Design Contradiction:
ProductivityVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical parameters of the catalyst system by switching from amine-based catalysts to nonhalogenated tin-based catalysts (such as dibutyltin dilaurate, dimethyltin diacetate, or dioctyltin dibutoxide). This parameter change eliminates the coloration issue while maintaining polymerization activity through the use of a diketone-based reaction rate controlling agent.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent introduces a diketone-based reaction rate controlling agent (such as acetylacetone, benzoylacetone, or di(4-bromo)benzoylmethane) as an intermediary substance that mediates between the nonhalogenated tin-based catalyst and the polymerizable composition. This intermediary controls the reaction rate and enables the use of nonhalogenated catalysts without sacrificing polymerization efficiency.

Inventive Principle:
Principle #24Intermediary (Mediator)

2Object-affected harmful factors

If nonhalogenated tin-based catalysts are used to eliminate toxicity, then safety is improved, but pot life becomes insufficient and quality stability deteriorates

Engineering Contradiction:
ImprovetoxicityVSAvoidpot life
Core Design Contradiction:
Object-affected harmful factorsVSDuration of action of moving object

Solution Approach 1:

The patent changes the reaction kinetics parameters by introducing a diketone-based reaction rate controlling agent that slows down the polymerization reaction at low temperatures. This allows nonhalogenated tin-based catalysts to provide sufficient pot life (several hours to tens of hours) while maintaining quality stability throughout the polymerization process.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The patent implements a periodic temperature elevation strategy where the polymerization is carried out by gradually elevating temperature from low to high over several hours to tens of hours. The diketone-based reaction rate controlling agent enables this extended periodic process by maintaining stable reactivity throughout the temperature transition, ensuring sufficient pot life and quality stability.

Inventive Principle:
Principle #19Periodic action

3Stability of the object's composition

If halogenated tin-based catalysts are used to ensure sufficient pot life and stability, then process stability is improved, but human health safety deteriorates due to high toxicity

Engineering Contradiction:
Improvepot life and quality stabilityVSAvoidtoxicity
Core Design Contradiction:
Stability of the object's compositionVSObject-affected harmful factors

Solution Approach 1:

The patent changes the chemical composition parameters by replacing halogenated tin-based catalysts with nonhalogenated tin-based catalysts. The introduction of a diketone-based reaction rate controlling agent compensates for the lower inherent stability of nonhalogenated catalysts, maintaining sufficient pot life and quality stability without the toxic side effects of halogenated compounds.

Inventive Principle:
Principle #35Parameter changes

Solution Approach 2:

The diketone-based reaction rate controlling agent serves as an intermediary that enables the use of nonhalogenated tin-based catalysts by modulating their reactivity. This intermediary substance allows the system to achieve the stability and pot life characteristics of halogenated catalysts while eliminating their toxicity, making the process both safe and stable.

Inventive Principle:
Principle #24Intermediary (Mediator)

Applied Scientific Principles

This section explains which scientific principles are used to turn an abstract innovation direction into a practical engineering solution.

Function Achieved in This Case

The solution provides a stable pot life, improved reactivity, and transparency, preventing bubble generation and optical nonuniformities, while being harmless to humans, suitable for manufacturing various plastic lenses like eyeglass and camera lenses.

Implementation Method 1

a catalyst having a strong polymerization activity may be used, or an increased amount of a catalyst may be used

Methodology Applied
Scientific EffectCatalysis: Catalysis

Implementation Method 2

the polymerization reaction is carried out over several hours to tens of hours while the temperature is gradually elevated from a low temperature to a high temperature

Methodology Applied
Scientific EffectHeating: Heating

Data Source

PatentEP3357950B1Polymerizable composition for plastic lens and method of preparing plastic lens using same
Publication Date: 2022.01.12 SKC CO LTD
  • EP3357950B1 patent drawingFigure 1~2
  • EP3357950B1 patent drawingFigure 3~4
  • EP3357950B1 patent drawing

AI summary

An embodiment relates to a polymerizable composition for a plastic lens. The polymerizable composition for a plastic lens according to the embodiment comprises a nonhalogenated tin-based catalyst and a diketone compound as a low-temperature reaction rate controlling agent. Accordingly, the polymerizable composition has a more stable pot life so that the polymerization rate can be appropriately controlled, thereby improving the reactivity and the workability, and that the generation of bubbles are prevented, thereby improving the transparency of the resin.